SimplySailingOnline.com shows by example how easily you can eliminate stress, become more independent, raise your children in a safer environment (while spending more time with them, instilling values not based on the mighty dollar) and avoid the traps of commercialism. Because we live and sail simply, we have been wandering for 11 years with no intention of stopping. This is not a trip for us; it is our life, and I hope to share our success with stories of laughter and tears, as well as how-to tips and DIY projects for preparing, sailing and making a boat a home, so that others can join us.

Financing the Dream: Part 2

October 5, 2015

A while ago I wrote a post about the various ways we have seen cruisers finance their sailing dream. While the post was informative and gave many options for readers to explore, it seemed to leave some of you wanting more. More details, more examples, more solid numbers to base your own futures upon. So here are some very specific examples of just how easy it is to work your way through paradise if you set yourself up to be marketable, look in the right places, and are willing to jump at opportunities when they present themselves.

Want that port gone?

During the year that we lived aboard before we left to go cruising, while I was fulfilling the rest of a contract and we were finishing the necessary components of the To Do list, I knew I had to get a marketable skill quickly. Dave had been working on boats (ours and customers') for six years and had acquired the skills and confidence to do most anything on a boat. I, on the other hand, had been a high school teacher for the previous 11 years: not a skill that traveled very well to faraway places where we planned to stay only a few months at a time. So I made the logical connections: boats = water = bars. I signed up for a bartending school and within a few weeks felt I had the confidence to fake my way into a job, even if I didn't have the necessary experience. (I later proved to be correct in that assessment.) I worked part time after school in a local restaurant to at least get some previous experience to put on a resume, and then we headed south.

Dave can do it.

I worked at several restaurants along the way: in Solomon's Island, MD; Islamorada, FL; and Baltimore, but summer 2004 found us broke again, in north Florida, not comfortable getting too much farther south in hurricane season, and running out of options. Which caused us to do something we had never contemplated before. We looked for work in a location that had no nearby anchorage. We would have to earn not only a month's living money and save a month's traveling money, but we had to add dockage to the equation, too. Intentionally or not, Dave set us up to fail.
"We will pay for one night. We've got 24 hours. If we both have jobs that seem like they'll put enough money in the bank after dockage, we'll stay. But the first month we don't earn that much, we leave."
It was 3:00 p.m. We paid for one night's dockage, took showers, wished each other luck, and headed off to see what we could find for work. I took my resume into the local restaurant and immediately encountered a prejudice I had never experienced before.

Somehow, working here hardly seemed like work.

"I would really like to hire you, and I'll recommend you to the owner, but, well, he has a rule. He doesn't hire boaters."
We'll see about that. I met Billy in his office, convinced him I wasn't just any boater, and was on the schedule for the following night before my hair had even dried from the shower.
When I went in search of Dave, I found him behind a sewing machine at the local canvas shop. He had not only gotten the job, but the owner had asked if he would work out the rest of the day. We were in. For that work stop, we needed to make (combined) $1,500 a month to live on, $1,500 a month to save, and $400 a month dockage. We made it every month until the kitty was full and it was time to head off in November. Rarely have I ever worked anywhere that I don't make $100 a shift. (In the Florida Keys it was closer to $300 a shift.) If you're willing to work a few doubles, pick up extra shifts, and basically work your ass off for 6 months, earning enough money to take the next 6 months off is rarely difficult.

That's fine in this country, you might think, but what about once you get to the Caribbean? There are plenty of islands on which an American can work legally, and even more places where you can work under the radar if you're willing to take your chances. We never worked illegally because we had three kids. You show up on an island with three boys and EVERYONE knows who you are and what you're doing, so sneaking around isn't an option. Therefore, we chose to stay on a US island, specifically St. Croix, for our winter work stops and travel to other islands during our 6 months of off time. I had a reader comment, "If I work once I leave the country, I'll be making the local starvation wage. I can't live on that." When we are in St. Croix, Dave charges $60 an hour for sail and canvas work, and at that rate he usually has a 6-week back log. Hardly a starvation wage. And if you can't make $600 a week tending bar in the islands, you're doing something seriously wrong.

But there is something even more important than having the right skills and being in the right place. More than anything, you must have the right attitude. If you think you can't make enough to live on in the Caribbean, well then, you're probably right. Stay on that gerbil wheel. But if you want to give it a shot, being ready to jump at any opportunity that presents itself will pay you great dividends.

A couple of days out of Panama, we were trying to eyeball our way into Albuquerque Cays since even up-to-date charts are based on 1800s data, when an anchored boat hailed us to let us know how they had managed to wiggle between the coral heads. After we anchored, Dave got on the radio to thank them for the hints. I heard Feisty ask, "Where are you headed?"
Dave stuttered, "Umm, we're really not sure. What about you guys?"
"Well, we're going to the Florida Keys to get some boat work done. You don't happen to know a good yacht carpenter in Marathon, do you?"
Dave looked at me and said, "You want to go to the Keys?"
"Uh, I guess, yeah. We've got to go somewhere."
He keyed the mic, "As a matter of fact, I'm a yacht carpenter, and we had discussed going to the Keys ourselves."
Yeah, 10 seconds ago.

Feisty turned out to be one of Dave's best customers. He worked on their boat for the next several months, in Mexico, Marathon, and then Ft. Lauderdale.

My point is whether you think you can or you think you can't, you're right. Can you leave the rat race before you get a fat retirement and just work as you go? Absolutely. Or at least, you can if you want to badly enough.

MONDAY we'll talk about those sailors who seem to do everything all wrong, but somehow make it out all right. Most of the time.